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WO 2007/079162 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date (10) International Publication Number 12 July 2007 (12.07.2007) PCT WO 2007/079162 Al (51) International Patent Classification: (74) Agent: REHBERG, Edward, F.; E. I. Du Pont De C07D 261/04 (2006.01) AOlN 43/80 (2006.01) Nemours And Company, Legal Patent Records Center, C07D 413/12 (2006.01) C07D 401/04 (2006.01) 4417 Lancaster Pike, Wilmington, DE 19805 (US). C07D 417/12 (2006.01) AOlP 17/00 (2006.01) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (21) International Application Number: AT,AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, PCT/US2006/049459 CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, (22) International Filing Date: JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, 28 December 2006 (28.12.2006) LT, LU, LV,LY,MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, (25) Filing Language: English RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 60/755,247 30 December 2005 (30.12.2005) US GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 60/839,988 23 August 2006 (23.08.2006) US ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), 60/857,307 7 November 2006 (07. 11.2006) US European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV,MC, NL, PL, PT, (71) Applicant (for all designated States except US): E. I. DU RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, PONT DE NEMOURS AND COMPANY [US/US] ; 1007 GN, GQ, GW, ML, MR, NE, SN, TD, TG). Market Street, Wilmington, DE 19898 (US). Published: — with international search report (72) Inventors; and — before the expiration of the time limit for amending the (75) Inventors/Applicants (for US only): LAHM, George, claims and to be republished in the event of receipt of [US/US]; 148 Fairhill Drive, Wilmington, DE Philip amendments 19808 (US). SHOOP, Wesley, Lawrence [US/US]; 500 Auten Road #3A, Hillsborough, NJ 08844 (US). XU, For two-letter codes and other abbreviations, refer to the "G uid Ming [CN/US]; 25 South Perch Creek Drive, Newark, DE ance Notes on Codes and Abbreviations" appearing at the beg in 19702 (US). ning of each regular issue of the PCT Gazette. (54) Title: ISOXAZOLINES FOR CONTROLLING INVERTEBRATE PESTS (57) Abstract: Disclosed are compounds of Formula (1), including all geometric and stereoisomers, yV-oxides, and salts thereof, Formula (1) : wherein A , A , A , A , A and A are independently, selected from the group consisting of CR and N; provided that at most 3 ofA , A , A ; A , A and A is N;B , B and B are independently selected from the group consisting of CR . andN; each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfo?yl, C1-C6 alkylamino, C2-G6 dialkylamino, -CN or -NO2; and R , R , R , R , W and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention. ISOXAZOLINES FOR CONTROLLING INVERTEBRATE PESTS FIELD OF THE INVENTION This invention relates to certain isoxazolines, their iV-oxides, salts and compositions suitable for agronomic and nonagronomic uses, including those uses listed below, and methods of their use for controlling invertebrate pests such as arthropods in both agronomic and nonagronomic environments. BACKGROUND OF THE INVENTION The control of invertebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, turf, wood products, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action. PCT Patent Publication WO 05/085216 discloses isoxazoline derivatives of Formula i as insecticides wherein, inter alia, each of A1, A2 and A3 are independently C or N; G is a benzene ring; W is O or S; and X is halogen or C1-C6 haloalkyl. SUMMARY OF THE INVENTION This invention is directed to compounds of Formula 1 including all geometric and stereoisomers, iV-oxides, and salts thereof, and compositions containing them and their use for controlling invertebrate pests: wherein A1, A2 , A3, A4 , A5 and A6 are independently selected from the group consisting of CR3 and N, provided that at most 3 of A1, A2 , A3, A4 , A5 and A6 are N; B 1, B2 and B3 are independently selected from the group consisting of CR2 and N; W is O or S; 1 R is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl or C -C7 cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R6; 2 each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C 1 C6 alkylsulfmyl, C1-C6 haloalkylsulfinyl, C 1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino, C -C6 dialkylamino, C2-C4 alkoxycarbonyl, -CN or -NO2 ; 3 each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3 C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C 1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C haloalkylsulfonyl, C1-C6 alkylamino, C2-C6 dialkylamino, -CN or -NO2 ; 4 R is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4 -C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C -C alkylcarbonyl or C2-C7 alkoxycarbonyl; 5 10 11 12 1 R is H, OR , NR R or Q ; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl or C4-C7 cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R7 ; or R4 and R5 are taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, said ring optionally substituted with 1 to 4 substituents independently selected from the group consisting of C1-C2 alkyl, halogen, -CN, -NO2 and C1-C2 alkoxy; 6 each R is independently halogen, C1-C6 alkyl, C1-C6 alkoxy, C 1-C6 alkylthio, C 1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, -CN or -NO2; 7 each R is independently halogen, C 1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C 1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C 1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C2-C7 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkylcarbonyl, C2-Cj haloalkoxycarbonyl, C2-C7 haloalkylaminocarbonyl, 2 C3-C9 halodialkylamϊnocarbonyl, hydroxy, -NH2, -CN or -NO ; or Q ; 8 each R is independently halogen, C1-C6 alkoxy, C -Cg haloalkoxy, C -C alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C 1-C haloalkylsulfonyl, C -C6 alkylamino, C -C6 dϊ alkylamino, C2-C4 alkoxycarbonyl, -CN or -NO2; 9 each R is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, Cj-C 6 haloalkoxy, C 1-C6 alkylthio, C 1-C haloalkylthio, C 1-C6 alkylsulfinyl, C 1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C 1-C6 haloalkylsulfonyl, C1-C6 alkylamino, C2-C6 dialkylamino, -CN, -NO2 , phenyl or pyridinyl; 10 R is H; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl or C4-C7 cycloalkylalkyl, each optionally substituted with one or more halogen; 11 R is H C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkylcarbonyl or C2-C7 alkoxycarbon yl; 12 3 R is H; Q ; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl or C4-C7 cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R7 ; or R1 1 and R 12 are taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, said ring optionally substituted with 1 to 4 substituents independently selected from the group consisting of C1-C2 alkyl, halogen, -CN, -NO2 and C1-C2 alkoxy; Q 1 is a phenyl ring, a 5- or 6-membered heterocyclic ring, or an 8-, 9- or 10-membered fused bicyclic ring system optionally containing one to three heteroatoms selected from up to 1 O, up to 1 S and up to 3 N, each ring or ring system optionally substituted with one or more substituents independently selected from R8; each Q2 is independently a phenyl ring or a 5- or 6-membered heterocyclic ring, each ring optionally substituted with one or more substituents independently selected from R9 ; Q3 is a phenyl ring or a 5- or 6-membered heterocyclic ring, each ring optionally substituted with one or more substituents independently selected from R9 ; and n is 0, 1 or 2.
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